Insurance Workers Share The Craziest Claims People Have Made

Life can throw some pretty absurd situations at you. When everything goes awry, who do you turn to when the time comes to repair the damage? Insurance agents, that’s who. People will come asking for money from their insurance company for everything from a stolen car to a trailer full of gold, making arguments that sometimes sound as though they came straight out of a fairytale.

From the comfort of their desks, insurance agents are yelled at, threatened, and even just straight up lied to. It’s a good thing they’re able to smell a fraud when they hear one – and most of the time they can laugh about it after. Here, insurance agents share some of the craziest insurance claims they’ve ever heard people make…

Roofless House

When I worked for a fire and water damage restoration company, we showed up to a job where a guy was trying to add a second story to his house, and hired some guys for the job. When the guys finished working the day before, they left the roofless house completely uncovered and it rained that night, soaking the entire house. Insurance covered it.

We spent the day cutting and pulling out soaking-wet carpet. That night, I kid you not, they didn’t cover the house again, and it rained again. Insurance covered that too. When we talked to the adjuster she said the claim was in the hundreds of thousands of dollars, and these people were basically getting a new house. I haven’t seen that much stupidity rewarded that well in a long time. Reddit user: dinosaur_chunks

Not Her Car

I worked in a car insurance call center and had a woman who wanted to make a claim for her crashed vehicle. Standard stuff except the registration number we had on our system was totally different than the car she was driving. She got really aggressive on the phone saying, “I told you the exact car I drive and the registration, you idiot!”

So we looked into it and eventually my team leader actually dug out, from the archives, the telephone recording from when she took out insurance with us. In it, the operator slowly repeats the car model and registration and says “is that correct” to which she replies “yes.” Busted. She wouldn’t give up so we sent her a CD with the recording. Reddit user: letomg0

Hit His Own Car

I once had a guy who drove a Bobcat while he worked for a construction company. He wasn’t paying attention one time, and backed the Bobcat into his own personal car. He made a claim for insurance, but technically, insurance covers the owner of the vehicle, not the person driving the vehicle, so the owner of the construction company was liable.

The owner was very angry, and tried to get out of it. He argued that hitting your own car was an easy way to get free insurance money, and claimed that the worker had done it on purpose. In the end, he couldn’t get out of it, and the owner was forced to pay the worker for hitting his own car. Rules are rules. Reddit user: Lambchops_Legion

Conspiracy Theorist

I had one guy who was extremely paranoid, and thought he was being followed by the FBI. He was driving and when he turned left, the car behind him also turned left; he jumped into the passenger seat, and then jumped out of the passenger seat’s door, and rolled into a ravine while the truck he’d been driving smashed into two other cars.

I talked to the person who was driving behind him, and he was obviously extremely confused. I simply couldn’t stop laughing while getting his account of what happened. Imagine watching the driver in front of you turn around, see you, look terrified, then jump right out of his moving vehicle. It was absolutely absurd. Reddit user: tsim12345

Stolen Tires

I had an elderly lady tell me that her bridge partner was so jealous of the new tires that she got on her car that she’d had her son steal the tires. She told me it happened in a grocery store parking lot while she was in the store. I asked her how she got home after this happened, and she said she drove. Huh?

When I explained to her that her story didn’t quite add up, she told me that they stole the tires, but replaced them with the same type of tires – only they just weren’t as new as hers had been. She was so convinced this was exactly what happened that she almost talked me into believing it could be true! Reddit user: dnedad585

The Borrowed Truck

I once investigated a reported stolen truck. The guy reported it to the police, his insurer, etc. I explained to him that we have to wait thirty days to see if the vehicle is recovered. On day two, he calls back and tells me he found his car. The level of embarrassment as he explained what happened was palpable through the phone.

Turns out he’d gone over to his neighbor’s house to help do some work, and the neighbor had asked his dad if he could borrow the truck. His dad, being the nice guy he was, said to keep it as long as he needed to, and they both just forgot about it till his dad went over to the neighbor’s house to borrow something. Reddit user: [redacted]

Spirit Of The Tree

I used to handle claims for a telecom. One of their trucks went under a tree and knocked off a branch or two. The owner of the house where the tree was located wanted to make a claim for the spirit of the tree, as it’d been violated. She claimed that the tree spoke to her, and told her it’d been wounded.

She wanted like $250,000. I was just like, “Lady, it’s a stick. Are you serious?” This claim went on for months, but we ended up closing out the claim when her friend, who was a tarot card reader, told her that the tree told her that it’d forgiven the telecom company, and wanted her to move on. Reddit user: -Words-Words-Words-

An Unfortunate Flood

I work for a huge insurance company, and have dealt with a lot of claims from restaurants over my career. There’s one that was quite a bit different than most of the others. It was a restaurant downtown, literally in the middle of the city. Someone apparently flushed a Band-Aid down the toilet, and caused a huge flood in the staff bathroom.

Since they’re really busy during work hours, they only use the staff bathroom in urgent cases. Suffice to say, no one checked on it. Since the toilet was connected to the city’s water system, there was no shortage of water to flow out of that toilet. The flood didn’t stop for two days, practically filling the restaurant with sewage. Reddit user: supremeshirt

Maintenance Required

One time, I had a client asking if his home insurance company would pay to hire someone to clean the leaves out of his gutters. When I explained how insurance works – in the nicest way possible – the man fired back, “What’s the point of paying for insurance then? What do you expect me to do, walk around my house every month and inspect it to make sure nothing’s wrong?”

Uh … yes, yes I do. Stuff like this always annoyed me. This man wasn’t even elderly or disabled. In fact, he was in perfect health, and even worked for a construction company, so he was clearly able to do manual labor. He simply didn’t want to take care of his own property, and expected us to do simple maintenance around his house. Reddit user: CincyGamer

Caught In The Act

I used to work in claims for a company that rents vehicles out. I had a claim where a driver rented a vehicle and stated his vehicle lost its brakes and power steering, and crashed into two parked vehicles. He made the allegation that the rental vehicle was faulty, and accused the rental company of failing to maintain their vehicles.

His explanation sounded a little out there to me. I had the claim investigated for possible fraud, and sent it to an SIU investigator to look into it. Turns out, the driver’s prosthetic leg got caught between the pedal and the brake, making him unable to free it and stop the car. He was just too embarrassed to admit the truth. Poor guy. Reddit User: brotree

Breaking Down In Luxury

I work for a roadside assistance insurance company. You pay a small yearly fee, and you can call a rescue center for a tow truck in case your car breaks down. It’s really a form of mini travel insurance. Our company covers the towing of the car to the nearest mechanic, and up to $300 for a rental car, hotel or public transportation.

We had a customer who totally misunderstood how the insurance worked. He sent in a claim of $7,000 USD. It included hotel costs, rental car costs, restaurant visit, a flight, another restaurant visit, train tickets and ski pass costs, since they missed out on skiing. We covered $300 USD of that $7,000. It was kind of tragic. Reddit user: says_ikr_and_leaves

Deer In The Trunk

I work in auto insurance. In our town, collision with wildlife is fairly common, and the deductible on your insurance is waived as long as the estimator can confirm that wildlife was the cause. This is usually done by just advising the claimant not to wash the vehicle prior to showing up to their appointment so that the estimator can view the point of impact for proof.

Well one gentleman called in, and had already washed his car. When he was advised that if we couldn’t confirm wildlife was the cause, he may have to pay his deductible to have his repairs done, he was having none of it. So he showed up to his estimate with the dead deer in his trunk. I wish I was making this up. Reddit user: Aksent_HS

A Quick Turn Around

This woman gets into an accident in her vehicle but doesn’t have collision coverage. At the crash site she calls our office to quickly add on collision insurance. Then, maybe an hour later, calls again to make the claim for the accident. Obviously, they spot the issue pretty quickly, but kick it down the line for us to tell her.

I explained to her in the nicest way possible that adding collision coverage after an accident, and then calling in the claim, was against company policy. She got livid, and started screaming at me. Fortunately, my boss decided to take over. I didn’t hear the rest of her side, but I did hear him say, “Ma’am, I’m sorry, but you’ve committed insurance fraud.” Reddit user: nocliper101

Taking The Jet To The Game

I’m an aviation insurance broker. We had a client who landed his jet in a field, called the police, and then left with his passengers to go to a football game. He was actually on the local news with his passengers, who were telling the story about how they got in a plane crash, and still managed to make it to the game.

The claims-handler ended up denying the claim. If memory serves me right, the claims-handler also found out the man had done something like this multiple times in the past, and so it was clear to him that this was an on-going scam. The man ended up suing our company for their settlement, but in the end, he wasn’t successful. Reddit user: morris9597

Mad Cow

I once had a claim where a man was attacked by his neighbor’s cow. The neighbor had actually moved quite a while before, but forgot one of his cows. Now when a cow is starving or dehydrated, I guess they go crazy, which is what happened to this one. The man was standing outside, getting his mail, when the cow began charging at him.

He ran to his house and tried to shut the door, but the cow beat him to it and ran inside with him. His wife then attempted to help get the cow out of the house, and was apparently injured in the process. The cow caused damages to the home, and injuries to the couple. Lesson is: don’t forget your cows when you move. Reddit user: claimsclaimsclaims

Cleared Out Yacht

I’m an adjuster in marine insurance. I once got a claim for a total loss on a 1.9 million dollar yacht. Apparently the boat was too deep to try and salvage. I thought it was odd that only the owner was on board when it sunk, and was rescued by the Coast Guard, so I hired a company who could check the wreck with an ROV sub.

Well, as it turns out, the boat was completely stripped of everything. Even stuff that couldn’t have floated away, like a TV and appliances, were all gone. I presented the owner with the entire video evidence and rejected the claim. If you’re going to scuttle your own boat, my suggestion is to do it over the Mariana Trench. Reddit user: disrespectful

A Painful Shower

I had a lot of crazy claims when I worked for insurance companies, but the one that sticks out in my mind was a building defect claim. A brand new home was being built, and the shower was supposed to have a fan installed, but it hadn’t been put in yet. As it was in the process of being completed, it had live wires hanging out.

A couple had moved in even though the house wasn’t complete. One day, the man was taking a shower even though the wires were exposed from the ceiling. He must have reached up for some reason at one point. He touched the wires and was severely electrocuted. I don’t understand why he would go ahead and touch those wires, as opposed to calling the builder to see what’s going on. Reddit user: Budge-O-Matic

One Deer, Three Cars

I had a client who was driving at night when a deer ran out in front of him. He slammed on his breaks, narrowly avoiding it, but another car coming the other way wasn’t so lucky and hit the deer a few feet further down the road. From the momentum, the deer flew onto my client’s car, crushing his radiator, hood, windshield, driver’s side door, and window.

My client’s truck tipped off the road and landed on its side, where he proceeded to wait while emergency workers came to remove the deer, which was attached to his door. What makes this crazier is that the same thing happened minutes later, and another vehicle joined my client in the ditch, with the same story, just a different deer. Reddit user: Jokerthewolf

Ran Over Cell Phones

We’ll sometimes get clusters of cell phone claims. This one time a guy at a fire station accidentally dropped his work phone while he was on an emergency call, and the phone was completely shattered and useless. Since he was on duty when it happened, we had no choice but to cover the cost of replacing the phone for him.

Within days of him receiving his new phone, half the employees from the same department “accidentally” ran over their cell phones while backing up the aerial truck. Oddly enough, the latest model mobiles seem to be immune to damage. We know exactly what’s going on, but without video evidence of them deliberately damaging their phones, we have no choice but to pay the claims. Reddit user: insurancestories

Thumbless

When I was a life insurance agent, a client called us because her husband had gotten into an accident during work, and lost his thumb. He had a death and dismemberment insurance policy with us, and his wife wanted to know if there was any way to claim it. So we had the company auditors have a look into his case.

Turns out the hospital concluded the wound was too clean to be an industrial accident. We checked with the husband’s employer, who confirmed no one witnessed the accident. They pressed and pressed him until he confessed that he actually cut his own thumb off with a knife, hoping for a payout. In the end he was thumbless, without insurance, and ended up getting a divorce. Just brutal. Reddit user: assesundermonocles

Hurricane Conveniences

I worked for a car insurance company during Hurricane Sandy. During that time, it became very clear to me and my coworkers that many people had purposely parked their vehicles where they knew there would be water damage, so that they could easily make a claim and get new cars when the hurricane ended.

One guy decided to follow this trend, but was nervous that the plan wouldn’t work, which would leave him with no insurance money. His genius idea to ensure that it’d work out was dumping cans of sardines in the back of his car. His reasoning was that the sardines would give it the appearance that salt water had washed throughout the car. Nope. Reddit user: uhhwhut

Inverted Hail

One guy had his car insured for all kinds of things, and a few years ago there was a pretty intense hail storm in the area where he lived. His car was conveniently in the garage, so it was safe from the hail stones. But since it was quite old, he saw an opportunity to use insurance money to get a new car.

He thought he could cash in by hammering his car with a rubber hammer. Did so all over, but was too lazy to climb on top to hammer in dents on the roof. So he had the brilliant idea to just hammer the roof from the inside. Unfortunately, hail does not fall upward. It might be a surprise, but he didn’t get any money. Reddit user: knukkohed

Arson Then Pizza

I had a lady straight up light her own house on fire, and then walk up the street to go get a slice of pizza. Her neighbor called the fire department, but by the time they arrived the house was a total loss. The lady started acting really crazy in our office, denying everything we said, and incessantly blaming the fire on an accident.

The adjusters from our company went to the house, and there was a bunch of evidence all pointing to the fire being arson. Eventually, the lady just confessed, but then she immediately fled down to Florida and last I knew was on the run from the cops, and the insurance company, for a variety of reasons. Reddit user: mmmmpork

A Quick Escape

I had a guy who worked for an auto manufacturer who was driving drunk one day. He went into oncoming traffic and hit a semi truck head on. He hit it in such a way that the driver’s side of the car was sheared completely off. The accident photos looked like someone had peeled the car open from front to back.

Somehow, this guy managed to jump into the passenger seat before impact, and then ran from the scene. He made it home before the police contacted him, and pretended that someone stole his car. They couldn’t get him on a DUI because he could’ve started drinking after the fact, but they did get him on leaving the scene of an accident. Reddit user: ArtG4536

Traveling House

When I worked in car insurance, there was a woman who was in a car accident, and emailed us the list of items apparently damaged in the car crash. I printed the list out and it was nearly two pages long, completely filled up. It had things like a wide screen TV, air conditioner units, and even custom Nike trainers.

The list would have filled a small truck. She claimed she was in the process of moving, which is why it was all in her car. Somehow all this was destroyed, but the car wasn’t a write off – it was just a little fender bender. Also, she drove a teeny tiny Miata! Who knows why, but they paid her out. Reddit user: [redacted]

A Life-Saving Collision

There was one man who had a really bad accident. He choked on his breakfast while driving, and passed out from asphyxiation. Unconscious, he drove onto the other side of the road, right into oncoming traffic, and took out a telephone pole, two parked cars, a Bobcat, and a barbed wire fence, which wrapped around his front axle and yanked it out.

When the paramedics arrived, they explained that hitting all those things did the Heimlich maneuver on him, causing him to choke up his breakfast and save his life. He walked away with one chipped tooth, and that was it. Not even a scratch on his body. Our insurance company, on the other hand, had to pay a huge chunk of money for all of the damage. Reddit user: roxinova

Reverse At A Stoplight

I had one where a guy was claiming injury, saying he was a passenger in a car that my insured backed into at a stop light. Leaving aside the obvious question – who backs up at a stop light – his case wasn’t helped by the fact that my insured, and the person whose car the “injured” party claims he was in, both denied this accident ever occurred.

When I confronted the man with the accounts of all of the other parties, proving to him that he was clearly lying to me, he just left it and never got back to me again. A lesson to be learned: if you’re going to attempt insurance fraud, make sure at least one of the other people in your car has your back. Reddit user: YourSpoonIsTooSmall

Double Car

One lady stands out for sure. She had two of the same vehicle, only insured one of them, and would just keep the insurance cards from the one vehicle she insured in both vehicles. She did this for years before getting caught when she hit someone in the vehicle that didn’t have coverage on it, and totaled both vehicles.

She gave police the insurance card at the scene of the accident, and obviously the VINs didn’t match. She tried to explain to us that we’d put in the wrong VIN when we insured it. Conveniently, she had the same year, make, and model of vehicle sitting in her driveway. She couldn’t seem to explain that one. Reddit user: WanderlustWannabe

Excessive Chiropractic

I spoke to a claimant who got into a very minor fender bender with our insured. She said that her neck was bothering her a bit after the accident, and would like to see a chiropractor to get an adjustment. We have no problem paying out for a couple of checkups with a chiropractor; as a matter of fact, it’s pretty standard.

What’s not normal is that she turned in a claim for almost one hundred visits over the course of a couple of months. All to the same chiropractor. I explained to her that we wouldn’t cover this, which seemed to perplex her. The chiropractor turned out to be her brother-in-law, which we discovered because they had the same last name. Very sly. Reddit user: got-to-be-kind

Legally Dead

I had a claim from a woman involving my insured. In the process, I was having trouble reaching my insured, so our validations team – the people who check that your insurance is legit when you take it out – found that the man in question was linked to a policy for someone who had been declared legally dead several years before.

They were eventually able to track him down, and sure enough the guy wasn’t dead. It turns out he somehow managed to get himself declared dead so he could…avoid junk mail. I suppose they won’t contact you if you’re not alive. He straight up got mad at our team because they found him, and he didn’t want advertising calls anymore. Reddit user: [redacted]

Phone On Fire

I had one guy give us a call because when he plugged his phone in, it immediately caught on fire. He asked if it was normal, to which I obviously said no. Eventually, after a few questions, I heard the fire alarm go off on his line, and realized that he meant that his phone was currently on fire.

I asked if he was okay, and he said that the fire had spread to the wall. I told him to hang up immediately and call 911. Pretty calmly, he insisted on asking, “Am I able to get a replacement phone?” I told him to worry about that later, and call 911 now. I wonder how he even made the call. Reddit user: popemichael

Cigars

There was one client who bought a box of really expensive cigars. He insured them against pretty much every possible accident: theft, fire, natural disaster, etc. I wasn’t sure what exactly he thought would happen to these cigars. But anyway, later, he filed an insurance claim, claiming that the cigars had all been destroyed in a series of small fires.

It was very clear that the man had simply smoked all of the cigars. The insurance company went to court over this case, and lost. We were forced to pay the man something like $20,000 for his “loss”. But right after, we managed to sue him for arson. So his little scheme didn’t really work out in the end. Reddit user: Vovix1

Backyard Dirt-Bike

One time a client called to insure his dirt-bike under contents insurance. For those who don’t know what contents insurance is, it’s pretty much insurance for the stuff that you use inside your home. So I replied, “Sir do you use your bike inside the home?” and the guy says, “Yeah I got a dirt-track in the backyard.”

So I had no clue if this guy was telling the truth, or just totally lying to try to get some insurance. I wound up transferring him to a special department so that they could look into it. Apparently they searched his home on Google Maps and, lo and behold, he really did have a full-on track right in his yard. Reddit user: Devi-L

Not A Savings Account

I was a dental insurance representative. This poor older lady I talked to had gotten all of her teeth pulled and replaced with implants, which had cost her at least $2,000 each. She did this all over the course of just a couple of visits. When we got the claim, we paid the yearly max, which was $1,500.

She expected us to pay the whole $30,000 tab, and was very confused about why we couldn’t do this. She thought that since she hadn’t used her insurance over the last few years, she’d built up a fund over time, allowing her to use more now. I had to explain that this is not how insurance works, and that we were not a savings account. Reddit user: Peas_through_Chaos

Collision Exaggeration

There was a woman who tried to sue someone for a collision that occurred in a parking lot. It turned out that the “collision” was literally just a tiny bump from a vehicle moving at about five mph. If that’s not crazy enough, we later learned that she only filed the claim three years after the accident had even happened.

Also, all of the injuries that she reported from the collision were traced back to pre-existing injuries that we were able to find in her medical records. When we weren’t giving her the answers she wanted, she threatened our lawyers and got extremely angry. She also wanted us to give her a million dollars or so, which would only ever happen if she was severely crippled. Reddit user: 2Rare2Kill

Scooter In The Way

So this lady called in to report a claim against our customer. She had parked her scooter in the entryway of a parking lot for like two minutes as she walked inside the bank. Our insured was angry and didn’t want to wait for her to come back to leave the parking lot. So our insured apparently just ran her scooter over.

Now, you may be thinking that she deserved the damage to her scooter for parking in the entryway, but her claim was actually valid. Even if someone blocks your home driveway, you can’t just destroy their car to leave. You have to call and get it towed. It doesn’t matter if that vehicle happens to be a scooter. Reddit user: Corwinator

Fake Flat

I had a guy call up about making a claim on his home insurance. We checked his address but could not find it on our database. We asked him to provide some proof of his current residence, which he agreed to do. So he sent us a letter which had a print out of a picture of his flat, located above a shop front.

We thought the photo was a bit suspicious as missing addresses tend to only apply to new builds, and the shop was quite old. So we went to Google maps to look, and we found the exact shop with no flat over it. The guy had photoshopped a flat onto the shop in order to make a fraudulent claim. Reddit user: drukath

Stolen TV

I had a woman who made a claim for a 70″ TV that had been stolen from her house. The criminals had broken a window, climbed in, removed the huge TV from the wall, and left the same way. We very quickly caught her for fraud when we realized that her 70″ TV wouldn’t have fit through the window.

She claimed it went through at a certain angle, an argument that obviously didn’t help her case. She then thought since she hadn’t actually been paid off, it wasn’t yet fraud and she’d be let off, so she admitted she sold it and broke the window herself. Unfortunately for her, she was not off the hook. Reddit user: [redacted]

Damaged En Route

I used to work for a shipping company, helping people insure large items that they were shipping. I got a call from a lady who took out insurance with us for a couch that she was shipping across the country. She wanted to use the insurance for damage to the couch. The only problem was that the couch was still being shipped.

Though I tried to explain that this didn’t make sense, she was convinced that it was damaged, even without seeing it. It took a while to explain to her that I wouldn’t be able to make this claim for her. She became very frustrated with me, and insisted that her intuition told her that the couch had already been damaged. For sure. Reddit user: BadClaireDay

Trailer Of Gold

I had a claim where a guy said that when his trailer burned down, it had been full of thousands of gold bars, and demanded payment for their damage. Obviously this was extremely unlikely, but also, there’s a limit on monetary item coverage anyway, usually $1,500. The guy would not budge on his account of what happened, and made an issue of it.

I used to be a mathematician, so I took the value the guy was trying to claim, divided that by the volume of space that many gold bars would occupy, and determined that many gold bars could not physically fit inside the claimant’s mobile home. In the end, it became clear that the guy was obviously mentally ill, and we let him retract his claim. Reddit user: [redacted]